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Methanol → 1-Methyl-3-{N-[[beta-[3,4-bis(isobutyryloxy)phenyl]ethyl]]carbamoyl}-1,4-dihydropyridine

HRID 1199572
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1199572
FC(F)(F)C([O-])=O.[CH3:8][N+:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:37])[NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])=[C:21]([O:31][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])[CH:20]=2)[CH:10]=1.CO.C([O-])(O)=O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O.CCOCC>[CH3:8][N:9]1[CH:14]=[CH:13][CH2:12][C:11]([C:15](=[O:37])[NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26](=[O:30])[CH:27]([CH3:29])[CH3:28])=[C:21]([O:31][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])[CH:20]=2)=[CH:10]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 887MethanolHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 140504311-methyl-3-{N-[[beta-[3,4-bis(isobutyryloxy)phenyl]ethyl]]carbamoyl}-pyridinium trifluoroacetate

Produkt 1

HCID 140504301-Methyl-3-{N-[[beta-[3,4-bis(isobutyryloxy)phenyl]ethyl]]carbamoyl}-1,4-dihydropyridine

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 0.55 g (1 mmol) of 1-methyl-3-{N-[[β-[3,4-bis(isobutyryloxy)phenyl]ethyl]]carbamoyl}pyridinium trifluoroacetate in 50 ml of deaerated water containing 10 ml of methanol was extracted three times with 30 ml portions of ether. To the resultant aqueous solution was added NaHCO3 (0.25 g, 3 mmol) and 50 ml of ethyl ether and the mixture was kept under nitrogen. To this ice-cold mixture was added sodium dithionite (0.52 g, 3 mmol) and the mixture was stirred vigorously for 30 minutes. The ether layer was separated and the aqueous layer was extracted twice with ether. The combined ether extracts were washed with water and dried over sodium sulfate. Ether was removed under vacuum, leaving an oily product. NMR analysis confirmed that the product has the structural formula: ##STR1577##

Aufarbeitung

  1. customThe ether layer was separated
  2. extractionthe aqueous layer was extracted twice with ether
  3. washThe combined ether extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. customEther was removed under vacuum
  6. customleaving an oily product

Quellen und Nachweise

ORD-Eintrag
ord-0cbb49e52220409f92dc1da99c871158
Quelldatensatz
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04900837

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